In July 2023, Kyle Bancroft sat down with a reporter from The Windham Eagle to talk about the bar he'd just renamed. He'd bought the place three years earlier when it was still called Café Sebago, then rebranded it East Shore Tavern. Bancroft grew up in Raymond. "We believe everyone will like it here," he told The Windham Eagle.
As of June 2026, East Shore Tavern is closed. Not seasonal, not renovating. Permanently.
The closure is one change in Raymond this year. To put it in context, it helps to understand the town's seasonal calendar.
Raymond's seasonal calendar
Raymond's population swells every summer because of a piece of geography most visitors never think about: Frye Island sits in the middle of Sebago Lake, reachable only by ferry from a dock on Raymond Cape Road, and it has no bridge. The ferries run two boats a day through July and August, easing back to one boat on weekdays and two on Fridays and weekends through September and October, before the whole operation shuts down for the winter around the first Monday in November. When the island closes, so does everything built to serve it, including The Leap, the waterfront restaurant on Frye Island known for years as Frye's Leap Cafe. The Mosquito Ice Cream Shop, a seasonal stand famous locally for a dog-friendly flavor called the Poly Dog, closes around the same time.
Tassel Top Park runs on its own version of the same clock. The 35-acre park on Route 302, with roughly 900 feet of sandy beach on Sebago Lake, charges a day-pass fee through the season and shuts the beach down after Labor Day. What doesn't get talked about as often is what happens next: from November through March, the wooded loop trail behind that same beach opens back up, free, to anyone who wants to walk it. The beach closes. The woods don't.
None of this is a surprise to anyone who has lived through a Raymond fall before. The seasonal pattern follows roughly the same timeline each year.
| What changes | Summer | Fall / Winter |
|---|---|---|
| Frye Island ferry | Two boats daily, July-August | Down to one weekday boat through Sept-Oct; season ends around the first Monday in November |
| Tassel Top Park | Fee beach, roughly $6 a day, open through summer | Beach closes after Labor Day; wooded trail loop opens free to walkers Nov-March |
| The Leap (Frye Island) | Open as a waterfront restaurant | Closes with the island each fall |
| Mosquito Ice Cream Shop | Seasonal stand, open through summer | Closed for the season |
| East Shore Tavern, 1248 Roosevelt Trail | Open year-round until June 2026 | Closed permanently as of June 2026 |
East Shore Tavern differed from the seasonal businesses in the table: it operated year-round. Its listed hours ran Tuesday through Saturday until 1 a.m., and it offered a full bar, pool, darts, cornhole, and DJs three nights a week.
An address, not just a business
What makes the closure land harder is what the building at 1248 Roosevelt Trail represents. Before it was East Shore Tavern, it spent about 15 years as Café Sebago. Bancroft bought that business, ran it under its old name for a few years, then rebranded in February 2023. Together, those dates indicate that the address had hosted a restaurant or bar for close to 18 years before East Shore Tavern closed in June 2026.
In a 2023 interview with The Windham Eagle, Bancroft said he wanted to give Raymond "a place to go for fun and entertainment" after years of the building sitting as a quieter neighborhood diner.
Dining options in Raymond
Raymond has several dining options. Fishermen's Catch, a family-run seafood market and restaurant known for lobster rolls, is still on Route 302 year-round. So is The Beacon for pizza and subs, The Good Life Market for deli and grab-and-go meals, Rose's Old World Restaurant & Pizzeria, Sportsman's Kitchen & Keg, Pondicherry House, and A La Mexicana, part of a small Maine chain with a Raymond location. Current restaurant listings for the town also still show Lake House Tavern.
A fall hiking option
One fall hiking option is Rattlesnake Mountain, reached via the Bri-Mar Trail off Route 85. It's a 2.8-mile moderate hike with about 692 feet of elevation gain, roughly an hour and a half to two hours round trip, and it opens onto views over Panther Pond and Crescent Lake that get their own kind of reputation once the leaves turn. It is also, worth knowing before you drive out there, off-limits to dogs. That's a real point of friction for anyone used to bringing a pet along on a fall walk, since Tassel Top's own wooded trails are dog-friendly even while its beach requires a day pass. If your fall hiking plans include a leash, Rattlesnake isn't where that plan works.
A change in 2026
Most years, describing Raymond's fall means describing a rhythm: the ferry slows, the island quiets, the beach closes, the trails open back up, and residents settle into whichever restaurants stayed open through the winter. That seasonal pattern is unfolding again this year. One additional change is that East Shore Tavern closed permanently in June 2026. Unlike seasonal businesses, it will not reopen with the ferry in spring.
Raymond's trails and dining options remain part of its business mix.
If you're watching how a town's business mix shifts and wondering what it means for property values or timing near Sebago Lake, that kind of on-the-ground read is exactly what The Moulton Group tracks street by street in Raymond. Reach out if you want a local's read on what a season like this one actually signals.
